Throughout the day-long, citywide adventure, the brand snapped images at each pitstop to include in their Fall/Winter 2013 Lookbook. The use of neutral colors and variety of materials—ranging from tweed to wool—make these definite winter essentials for the final patch of cold weather.

Oh, and in case you were wondering, Matt won.

Check out each look Matt & Miles rocked for the Band Of Outsiders FW’13 lookbook in the following gallery: